Trifluoroacetic acid → methyl 2-({[1-(5-{[(2S)-2-aminopropanamido]methyl}thiophen-3-yl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]formamido}methyl)benzoate

Participants

Reaction Steps

Compound 15f (108 mg, 0.177 mmol) was shaken in a solution of DCM (0.7 mL) and TFA (0.3 mL) for 1 hour. The reaction was then diluted with DCM and concentrated under reduced pressure. More DCM was added to the residue and then removed again by reduced pressure. The residue was then dissolved in ethyl acetate and washed with saturated NaHCO3 (3×). The aqueous phases were combined and extracted with ethyl acetate. The organic phases were combined, washed with brine, dried over Na2SO4, filtered and concentrated to give the compound 9 h (89.3 mg, 99% yield) as a white crust. 1H NMR (CD3OD) δ(ppm): 7.97 (d, J=8.0 Hz, 1H), 7.56 (t, J=7.2 Hz, 1H), 7.46-7.44 (m, 2H), 7.41 (t, J=7.6 Hz, 1H), 7.12 (s, 1H), 7.09 (s, 1H), 4.82 (s, 2H), 4.51 (d, J=15.6 Hz, 1H), 4.98 (d, J=15.6 Hz, 1H), 3.89 (s, 3H), 3.42 (q, 1H), 1.27 (d, J=6.8 Hz, 3H). LRMS (ESI): calc 509.1; found 510.1 (MH)+.

Provenance & Evidence